Water → 6-Bromo-4-chlorothieno(3,2-d)pyrimidine

HRID 2297753Notes

Reaction equation

C(NC(C)C)(C)C.[Li].[Cl:9][C:10]1[C:11]2[S:18][CH:17]=[CH:16][C:12]=2[N:13]=[CH:14][N:15]=1.[Br:19]C(F)(F)C(Br)(F)F.O>O1CCCC1>[Br:19][C:17]1[S:18][C:11]2[C:10]([Cl:9])=[N:15][CH:14]=[N:13][C:12]=2[CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In a 250 mL round-bottomed flask 65 mL of tetrahydrofuran and lithium diisopropylamine (18.5 mL, 37 mmol, 2M in tetrahydrofuran) were cooled to −78° C. 4-chloro-thieno[3,2-d]pyrimidine (5.26 g, 31 mmol) was dissolved in 37 mL of tetrahydrofuran and slowly added to the reaction mixture over 5 minutes, After 20 minutes 1,2-dibromo-1,1,2,2-tetrafluoroethane (4.05 mL, 34 mmol) was added slowly to the solution of the anion. The temperature was maintained at −78° C. for 20 minutes then warmed to room temperature for 2 hours. The reaction mixture was poured into water and extracted with chloroform (3×100 mL), dried over sodium sulfate, and dried in vacuo to afford 7.70 g (99%) of 6-bromo-4-chloro-thieno[3,2-d]pyrimidine. 1H NMR (400 MHz, DMSO) d 8.97 (s, 1H), 8.01 (s, 1H). LC-MS: 249, 251 (MH+); HPLC RT: 4.04 minutes.

Workup

additionwas added slowly to the solution of the anion
temperaturethen warmed to room temperature for 2 hours
extractionextracted with chloroform (3×100 mL)
dry with materialdried over sodium sulfate
customdried in vacuo

Sources & evidence

ORD record: ord-19014a377c5141a98cddec514b70d3bc
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492383B1

Reaction notes

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